Pyridine → HCID 121331756, compound

HRID 64151Notes

Reaction equation

HRID 64151 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([N:15]2[C:19]3=[N:20][CH:21]=[C:22]([Br:24])[CH:23]=[C:18]3[N:17]=[CH:16]2)[CH:12]=[C:11]([NH2:25])[CH:10]=1.N1C=CC=C[CH:27]=1.[CH3:32][N:33](C)[S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([N:15]2[C:19]3=[N:20][CH:21]=[C:22]([Br:24])[CH:23]=[C:18]3[N:17]=[CH:16]2)[CH:12]=[C:11]([N:25]([CH3:27])[S:34](=[O:36])(=[O:35])[NH:33][CH3:32])[CH:10]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 83372Dimethylsulphamoyl chlorideHCID 89500107HCID 89500107, compound

Product 1

HCID 121331756HCID 121331756, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2′,4′-difluoro-5-((6-bromo)-3H-imidazo[4,5-b]pyridin-3-yl)-[1,1′-biphenyl]-3-yl)amine (3.0 g, 7.48 mmol) in DCM (10 ml) was added pyridine (3 ml, 37.9 mmol, 2 eq.) followed by dimethylsulfamoyl chloride (1.6 g, 11.22 mmol, 1.5 eq.). The mixture was stirred for 16 h and quenched and extracted as in Example 1(d). The solvent was distilled off to afford the crude product which was purified by preparative HPLC to give the title product in 55% yield (2.1 g).

Workup

  1. customquenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off
  4. customto afford the crude product which
  5. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-66bddfe5de214a95a685821741f9e31a
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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